Triflusulfuron-methyl (Ref: DPX 66037)

Triflusulfuron-methyl (Ref: DPX 66037)	Last updated: 20/03/2021
(Also known as: triflusulfuron; IN 66037; T 478)

GENERAL INFORMATION

Description

A post-emergence herbicide for the control many annual and perennial broad-leaved weeds

Example pests controlled

Black bindweed; Charlock; Chickweed; Cleavers; Fathen; Field pansy; Fools parsley, Knotgrass; Redshank; Volunteer rape

Example applications

Sugarbeet; Fodder beet; Red beet; Mangolds; Chicory

Efficacy & activity

Triflusulfuron based products have been registered in many EU countries based on detailed national assessments of the efficacy package.

Availability status

Current

Introduction & key dates

1992

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France/Denmark

Date EC 1107/2009 inclusion expires

31/12/2021

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓			✓	✓	✓		✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓	✓	✓	✓	✓	✓	✓	✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
		✓	✓	✓	✓	✓		✓

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₇H₁₉F₃N₆O₆S

Canonical SMILES

CC1=CC=CC(=C1S(=O)(=O)NC(=O)NC2=NC(=NC(=N2)OCC(F)(F)F)N(C)C)C(=O)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

IMEVJVISCHQJRM-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H19F3N6O6S/c1-9-6-5-7-10(12(27)31-4)11(9)33(29,30)25-15(28)22-13-21-14(26(2)3)24-16(23-13)32-8-17(18,19)20/h5-7H,8H2,1-4H3,(H2,21,22,23,24,25,28)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

96%

Known relevant impurities

EU dossier - N,N-dimethyl-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine <10/g kg⁻¹; Dimethylcarbomyl chloride may also be present.

Substance origin

Synthetic

Mode of action

Selective, inhibits amino acid sysnthesis. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

126535-15-7

EC number

Not available

CIPAC number

731.201

US EPA chemical code

129002

PubChem CID

92434

Molecular mass

492.43

PIN (Preferred Identification Name)

methyl 2-({[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoyl}sulfamoyl)-3-methylbenzoate

IUPAC name

methyl 2-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoylsulfamoyl]-m-toluate

CAS name

methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

White crystalline solid

Related substances & organisms

lenacil

triflusulfuron

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Debut
Upbeet
Safari

Example products using this active

DuPont

Formulation and application details

Often supplied as water dispersible granules that are mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

260

at 25 °C

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

27000

Ethyl acetate

120000

Acetone

1.6

Hexane

17000

Methanol

Melting point (°C)

159

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

159

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

8.71 X 10⁰⁰

Calculated

Log P

0.94

at 25 °C

Low

Bulk density (g ml⁻¹)

1.46

Dissociation constant pKa) at 25 °C

4.4

Weak acid, 25 DegC

Vapour pressure at 20 °C (mPa)

1.01 X 10^-02

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

1.91 X 10^-05

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Acidic soln: 228nm=40300, 291nm=981
Neutral soln: 235nm=51700, 291nm=474
Basic soln: 235nm=51700, 291nm=481

Surface tension (mN m⁻¹)

67.92

at 20°C 98.9%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

14.6

Non-persistent

DT₅₀ (lab at 20 °C)

14.6

Non-persistent

DT₅₀ (field)

4.5

Non-persistent

DT₉₀ (lab at 20 °C)

48.4

Moderately persistent

DT₉₀ (field)

16.9

DT₅₀ modelling endpoint

6.1

normalised geometric mean

Note

EU 2019 RAR dossier lab studies (measured) DT₅₀ range 4-20.9 days, DT₉₀ (measured) range 19.5-69.3 days, Soils=11; Field studies DT₅₀ (normalised) range 3.7-6.2 days, DT₉₀ (measured) range 12.3-20.6 days, Soils =4; Other studies: DT₅₀ 2-4 days (F3)

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

13.9

Moderately fast

Note

pH sensitive: 3.8 days at pH 5, 24.6 days at pH 9

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Moderately persistent

Note

pH sensitive: 3.7 days at pH 5, 36 days at pH 9

Water-sediment DT₅₀ (days)

26.4

Fast

Water phase only DT₅₀ (days)

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

0.68

Mobile

K_foc

¹/_n

0.92

Notes and range

EU 2008 dossier K_f range 0.36-1.28 mL g⁻¹, K_foc range 25-132 mL g⁻¹, ¹/_n range 0.90-0.94, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.46

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

3.74 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

methyl saccharine (Ref: IN-W6725)

Soil

0.881

Major fraction, Relevant

N,N-dimethyl-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine (Ref: IN-D8526)

Soil

0.923

Major fraction, Relevant

N-desmethyl triazine amine (Ref: IN-E7710)

Soil

0.547

Major fraction, Relevant

N,N-bis-desmethyl triazine amine (Ref: IN-M7222)

Soil

0.317

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

N,N-dimethyl-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine (Ref: IN-D8526)
Note: Soil DT50 = 74–664 days

triazine amine

Soil (Aerobic)

N-methyl-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine (Ref: IN-E7710)
Note: Soil DT50 = 30–393 days

N-desmethyl triazine amine

Soil (Aerobic)

6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine (Ref: IN-M7222)

N,N-bis-desmethyl triazine amine

Rat; Plant; Soil (Aerobic)

triflusulfuron

Water/sediment

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1.3

Estimated

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 6.9

Rat

High

(ppm diet)

> 100

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

> 89.5

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1535 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

27.6

Colinus virginianus NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

730

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

10.0

Pimephales promelas

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 960

Daphnia magna

Low

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

11.0

Daphnia magna

Low

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.0025

Lemna gibba

High

Non-target plants

17.8

Grain sorghum
Vegetative vigour, ER₅₀
as g ha⁻¹

23.5

OSR
Seedling emergence, ER₅₀
as g ha⁻¹

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.034

Pseudokirchneriella subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

125

Eisenia foetida

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

120

>, as product ha⁻¹ (WG 50: Conc 50 g as/L)
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

120

>, as product ha⁻¹ (WG 50: Conc 50 g as/L)
Typhlodromus pyri

% Effect

Soil micro-organisms

Nitrogen mineralisation: No adverse effect
Carbon mineralisation: No adverse effect

Dose: 225 mg kg⁻¹ soil 56 days

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.1

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.025

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.15

Rabbit SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

0.09

Rabbit SF=100

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.04

Rat SF=100

Dermal penetration studies (%)

25-75

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

May affect body weight and food intake
Possible liver toxicant
USEPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Treat fires with water spray, foam, dry chemical or CO2

CLP classification 2013

Health: H351
Environment: H400, H410

EC Risk Classification

Carcinogen category 3: R40

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

triflusulfuron-methyl

French

triflusulfuron-methyle

German

Triflusulfuron

Danish

triflusulfuron-methyl

Italian

triflusulfuron-metile

Spanish

triflusulfuron-metil

Greek

Polish

triflusulfuron metylu

Swedish

triflusulfuronmetyl

Hungarian

triszulfuron-metil

Dutch

Record last updated:	20/03/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242